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270 7th Street, Saint James
$625,000
3 Beds ⋅ 2 Baths ⋅ 999669 MLS
Welcome to this charming 3-bedroom, 1 1/2-bath ranch perfectly situated on a spacious corner lot in the heart of highly desirable St. James and located within the acclaimed Smithtown Central School District. With inventory in St. James remaining extremely limited, this is an exceptional opportunity to own in one of Long Island’s most sought-after communities. Lovingly maintained over the years, this home offers the perfect blend of comfort, character, and endless potential to make it truly your own. Features include a functional ranch-style layout, 1-car garage, partial basement ideal for storage or future possibilities, and in-ground sprinklers for easy lawn maintenance. Step outside to enjoy the expansive yard — perfect for entertaining, gardening, outdoor gatherings, or simply relaxing in your own private retreat. Conveniently located near shopping, restaurants, parks, schools, and all local amenities, this home offers both tranquility and convenience in an unbeatable location. Whether you’re looking to settle into St. James for the first time, downsize, or create your dream home, this is an opportunity you won’t want to miss.

270 7th Street, Saint James

107 Fairfield Drive N Unit #107, Saint James
$610,000
2 Beds ⋅ 2 Baths ⋅ 921202 MLS
Welcome to Fairfield at Saint James! This beautifully renovated first floor unit in a desirable 55+ community offers modern comfort and peace of mind with brand-new 2024 upgrades throughout. The bright and inviting living area features new flooring, recessed lighting, and a sliding glass door with built-in blinds that opens to a private outdoor space. The kitchen has been completely updated with new cabinetry, quartz countertops, and stainless steel appliances, along with a full-size washer and dryer conveniently located in the utility closet. The primary bedroom features a private en-suite bathroom, fully renovated for a clean, modern look, while the second bath has also been thoughtfully refreshed. Enjoy new heating and air conditioning systems and a new 40-gallon hot water tank, providing efficiency and reliability for years to come. Residents enjoy access to an impressive array of amenities, including an outdoor and indoor pool, a fitness center, clubhouse, park-like grounds, tennis and pickleball courts—all maintained for a resort-style living experience. With a low HOA of $357 per month. Move-in ready and beautifully updated, this home offers the perfect blend of style, comfort, and convenience.

107 Fairfield Drive N Unit #107, Saint James

908 Drew Lane, Saint James
$599,000
2 Beds ⋅ 2 Baths ⋅ 968859 MLS
Rare End-Unit Ranch with Garage in the Desirable 55+ Community of Fairfield at St. James! This move-in-ready home offers comfortable and convenient living with a formal dining room and a spacious living room featuring sliders to the rear patio, where you can enjoy lush landscaped grounds, sunny southern exposure, and beautiful cherry trees! The updated kitchen features Silestone countertops, wood cabinetry, and a tile backsplash. Down the hallway, you’ll find a pantry/utility closet, updated full bathroom, and two generously sized bedrooms, including a primary en-suite, both with California Closet systems. The home is equipped with York central air conditioning and electric baseboard heating for year-round comfort. Additional updates include an updated electric panel, new carpeting, new vinyl flooring, a new dishwasher, and a new storm door. Residents enjoy outstanding amenities, including a clubhouse, indoor pool, two outdoor pools, fitness center, library, billiards, tennis, bocce, pickleball, and scenic walking trails.

908 Drew Lane, Saint James

1206 Gotham Drive, Saint James
$580,000
2 Beds ⋅ 2 Baths ⋅ 944933 MLS
Welcome to Fairfield at St James a 55+ senior community with country club style living! All on one floor— No steps. Enter through outdoor courtyard patio. Spacious two bedroom includes a master bedroom suite with changing room-walk-in closet- floor to ceiling closet and full bath. Two full tiled baths , one completely redone 2023. Very large living room with high ceilings and lots of windows for an abundance of natural light. Sliding door to patio which is very private ( no condo behind it) just beautiful treed area. Formal dining room with chandelier and large window. (Electric panel in DR). Eat in kitchen with cherry wood Shaker cabinets and under cabinet lighting -stainless steel appliance-Refrigerator is 3 years, granite countertops. Separate laundry room with hot water heater. Lots of closets. Wood laminate floors throughout with some tiled floors. Small outside attached storage area. New roof about 4 years.Common charges include water, basic cable, snow removal, and landscaping. Fairfield at St James country club living includes clubhouse, tennis courts, pickle ball, 1 indoor and 2 outdoor swimming pools, walking trails. Buses provided weekly for shopping. Many opportunities for outside trips, dinners, entertainment, club for card playing, and book club. Lovely grounds with peaceful, quiet atmosphere.

1206 Gotham Drive, Saint James

506 Drew Drive, Saint James
$560,000
3 Beds ⋅ 3 Baths ⋅ 970144 MLS
Welcome to easy living in this beautiful 3-bedroom, 2.5-bath condo located in the 55+ Fairfield at St. James sought-after community. This bright and spacious home features an updated kitchen, a mix of wood and carpeted flooring, and newer rear sliding door that fills the home with natural light. The home offers central A/C, many closets including walk-in closets, recessed lighting, and ceiling fans, providing both comfort and functionality. Step out back to your private patio and enjoy a beautiful, peaceful, picturesque views, perfect for relaxing with morning coffee. Additional storage area located outside. This desirable 55+ gated community offers many enjoyable activities; including both an indoor pool with spa and outdoor pool, tennis, pickle ball, recreation room and more. A perfect combination of comfort, style, and low-maintenance living in a welcoming community.

506 Drew Drive, Saint James

233 Cedar Street, Saint James
$550,000
2 Beds ⋅ 1 Baths ⋅ 936994 MLS
Opportunity awaits with this charming home is St. James. House sits on flat level .19 acres close to the heart of St. James with access to shops and the train station. Entire interior has been freshly painted. Upon entering the home you will walk into the living room that features a vaulted ceiling and windows that allow for plenty of light. The primary suite is a nice size that includes closet space and separate closet for the washer and dryer. The second bedroom is next to the Primary and has a vaulted ceiling. The kitchen off the living room has brand new stainless steel appliances with a back door leading to the rear yard. Other features include Hardwood flooring, recessed lighting and new cesspool with overflow installed in July of 2024

233 Cedar Street, Saint James

102 Gotham Way, Saint James
$550,000
3 Beds ⋅ 3 Baths ⋅ 901666 MLS
Welcome to 102 Gotham Way in a desirable 55+ community. This beautifully maintained home offers easy, low-maintenance living with a bright, open layout designed for comfort and everyday enjoyment. The main level features a spacious primary en suite, providing convenience and privacy, along with generous living and dining areas perfect for entertaining or relaxing. Large windows fill the home with natural light, creating a warm and inviting atmosphere throughout. Enjoy a vibrant active-adult lifestyle with access to community amenities, social activities, and beautifully landscaped grounds. Conveniently located near shopping, dining, parks, and major roadways, this home offers the perfect balance of peaceful community living and neighborhood convenience. A wonderful opportunity to enjoy carefree living in a sought-after location.

102 Gotham Way, Saint James

22 Hill Road, Saint James
$542,200
2 Beds ⋅ 1 Baths ⋅ 957742 MLS
Charming, warm and truly one of a kind, this very special storybook cottage is rich in character and classic, timeless details with a top, top location in North Saint James & nestled on the cusp of sought after Head Of The Harbor, close to the Saint James General Store, Route 25A Shopping, Schools, Stony Brook Village & just a short drive to Port Jefferson Village! Perfect as a year round home (with room for expansion) or a wonderful charming second home/summer getaway...The home offers two well sized bedrooms, immaculate full bathroom, a large great room (living room & dining room) with a striking stone fireplace taking center stage, beautifully framed by two stunning trapezoid shaped stained-glass windows that flood the space with warmth. Custom cabinetry & original details throughout including a hand carved front door, built in corner cabinet in the dining room (crafted by the homeowner), a cabinet lined kitchen, garage & large basement with ample storage, and meticulously manicured property wrapped in perennial gardens, stone walls, flowering bushes, perennials & trees. A rare and unique opportunity for those seeking craftsmanship, charm and an exceptional setting.

22 Hill Road, Saint James

8 Steep Bank Road, Saint James
$539,000
856145 MLS
Discover the perfect opportunity to build your dream home in the prestigious and picturesque Village of Nissequogue. This 2-acre parcel is situated at the end of a serene cul-de-sac, offering privacy and tranquility in one of Long Island's most sought-after locations. Key Features: - Approved DEC and Health Department permits for a 5,000 square-foot custom home. - Elevated lot, providing stunning potential views and a commanding presence. - Located just minutes from the breathtaking Long Island Sound, where you can enjoy pristine beaches, scenic views, and all the natural beauty the area has to offer. - Proximity to renowned vineyards, stables, and golf courses, ensuring a lifestyle of leisure and sophistication. Don't miss this rare opportunity to own a piece of Nissequogue's serene and scenic beauty.

8 Steep Bank Road, Saint James

1305 Gotham Court W, Saint James
$518,400
2 Beds ⋅ 2 Baths ⋅ 1015354 MLS
Lovingly maintained 2bd 1 1/2 bath unit located in the desirable Gotham section. Living room with 12ft ceilings and recessed lighting. Primary Bedroom suite, second bedroom with 1/2 bath. Completely updated , including new eat in kitchen with granite counter tops, stainless appliances ,updated baths with Primary bath walk in shower, new flooring, and custom closets. New Anderson windows and sliding glass door that leads to a beautiful patio area with new awning. Garage, which includes above attic storage with stair access. This unit is ready for you to move in settle down and enjoy. A few of the many amenities included in The Fairfield Community are a pool, tennis courts, and clubhouse just to to name a few.

1305 Gotham Court W, Saint James

707 Bentley Court, Saint James
$509,000
2 Beds ⋅ 2 Baths ⋅ 982741 MLS
Discover peaceful waterfront living in this well-maintained 2-bedroom, 2-full-bath condo situated directly on a serene pond. With only two buildings sharing the water view, the residence offers privacy and lasting vistas from every room. The spacious living/dining room combination creates an open, comfortable entertaining space, while the eat-in kitchen provides casual dining options. Recent updates include a newer roof, serviced central air conditioning, professionally cleaned carpeting and fresh paint in the main living area. Ideally located directly across from the clubhouse for easy access to community amenities. Low taxes and low common charges enhance the value. This active 55+ community rarely has waterfront units available—bring your finishing touches and make it your own.

707 Bentley Court, Saint James

604 Cabot Court E Unit #604, Saint James
$499,999
2 Beds ⋅ 2 Baths ⋅ 993563 MLS
Welcome to Fairfield at St James. This 55+ community features low taxes and green spaces with parkland, sidewalks, and pond, plus a Clubhouse with library, fitness center, billiards room, indoor pool, 2 outdoor pools, tennis and pickle ball courts. This 2 bedroom, 2 bath Condo is move-in ready. Enter the Condo and view a large front to back space with coat closet, Dining area and Living Room with sliding glass door to the patio that fill the room with natural light. Continue to the eat-in kitchen with light wood cabinetry, white appliances, a roomy space for table and chairs and a large window to enjoy the garden view. The hallway has fixed skylights that provide more natural light and acess to the pantry, the 2nd bedroom and the full bath with tub and shower. Next is the spacious primary bedroom with large windows, an adjoining dressing room with closets, a vanity with sink and door to a separate room for the shower and toilet.

604 Cabot Court E Unit #604, Saint James

901 Fenway Road, Saint James
$499,000
2 Beds ⋅ 2 Baths ⋅ 951936 MLS
Beautiful 2 bedroom, 2 bath lower-level 55+ condo located in the gated community of Fairfield at Saint James. This well-maintained one-floor unit offers an ideal blend of comfort and convenience. The spacious eat-in kitchen features ample cabinetry and plenty of natural light, flowing seamlessly into the formal dining and living room. Sliding doors lead to a private patio with peaceful greenery views, perfect for relaxing or entertaining. The primary bedroom includes a large en-suite bathroom and a generous walk-in closet, creating a comfortable retreat. A second bedroom, full bathroom, large hallway closet, and a laundry/utility room provide added functionality and convenience. Features 2 year old AC and hot water heater. Brand new roof. This highly desirable 55+ community offers an impressive array of amenities, including a clubhouse, tennis courts, two outdoor pools, an indoor pool, fitness center, library, and billiards room. Residents also enjoy access to convenient bus service for shopping. Ideally located near Smith Haven Mall, restaurants, a movie theater, and other everyday conveniences, this home is one you don’t want to miss.

901 Fenway Road, Saint James

260 Old Mill Road, Saint James
$499,000
856152 MLS
Build Your Dream Home in Spectacular and Peaceful Nissequogue Village. Building permit was issued on 12/9/25. Located in the heart of the serene and prestigious Nissequogue Village, this exceptional property offers the rare opportunity to bring your vision to life. Key Features: • Approved blueprints for a luxurious 5-bedroom, 5.5-bathroom home designed with modern elegance and functionality. • All permits in place, ensuring a smooth and hassle-free building process. • Nestled in a tranquil setting, perfect for those seeking privacy and natural beauty. This is your chance to create a custom masterpiece in one of Long Island's most coveted communities. With its stunning surroundings and proximity to beaches, golf courses, and fine dining, Nissequogue Village offers an unparalleled lifestyle.

260 Old Mill Road, Saint James

909 Fenway Road, Saint James
$490,000
2 Beds ⋅ 2 Baths ⋅ 966450 MLS
Stunning 2 Bedroom 2 Bath Renovated Upper Andover Model in the Highly Desired 55+ Fairfield @ St. James Gated Condominium Complex. This Andover Unit Renovation was Just Completed to Include a Remodeled Kitchen With New Stainless Steel Appliances, Recessed Lighting, Waterproof Laminate Flooring. All Doors, Hardware, Moldings, Electrical Outlets & Switches, Lighting Fixtures are New and Unit is Freshly Painted. Unit has Super Spacious Sized Rooms with Loads of Natural Light Coming in Through Updated Windows. Sliding Doors Lead to Private Covered Deck Area with Nice Wooded Views. There is a Separate Utility Room W/ Washer & Dryer, HVAC System, Hot Water Heater. HVAC System Serviced in December. Amenities Include Trips, Fitness Center, Indoor & Outdoor Swimming Pools, Billiards, Library, Tennis, Bocce, Pickleball, & Clubhouse Activities. LOW TAXES AND HOA!! COME SEE THIS GORGEOUS UNIT AND MAKE IT YOUR HOME!

909 Fenway Road, Saint James

704 Cabot Court W, Saint James
$490,000
2 Beds ⋅ 2 Baths ⋅ 911106 MLS
Welcome to 704 Cabot Court, a beautifully updated residence in the Fairfield at St. James, a gated 55+ community offering comfort, security, and an active lifestyle. This sun-filled home features 2 bedrooms and 2 full baths, including a spacious primary suite with ample closet space and a private bath. The open living and dining area flows seamlessly, highlighted by vaulted ceilings, large windows, and sliding glass doors that lead to a private patio—ideal for relaxing or entertaining. The kitchen offers a breakfast nook, generous cabinetry, Stainless steel appliances, and an efficient layout designed for convenience. Additional highlights include a separate laundry area, central air, and an attached garage with private driveway. The Fairfield at St. James community provides resort-style amenities including a clubhouse, fitness center, tennis, and a sparkling outdoor pool. Residents enjoy a vibrant social calendar, beautifully maintained grounds, and the peace of mind of a secure, gated neighborhood. Located in the heart of Saint James, this home offers close proximity to shopping, dining, golf, beaches, and major roadways. Experience the balance of comfort and community in one of Long Island’s most sought-after 55+ developments.

704 Cabot Court W, Saint James

201 Bentley Court E, Saint James
$477,500
2 Beds ⋅ 2 Baths ⋅ 963252 MLS
Welcome to Fairfield at St. James, a desirable 55+ gated community. This completely remodeled 2-bedroom (1 Bedroom was the dining room closed currently)., 1.5-bath ranch-style condo offers an open and spacious layout with gleaming hardwood floors throughout. The formal living room flows seamlessly into a modern kitchen featuring stainless steel appliances, stone countertops, and a detailed backsplash. The home includes a beautifully updated full bath and half bath, plus the convenience of an in-unit washer and dryer. Enjoy your own private, secluded patio—perfect for relaxing outdoors on warm summer days. Community amenities and low-maintenance living make this home a wonderful opportunity. Fairfield Community Amenities include a Clubhouse, 1 indoor pool and 2 outdoor pools, tennis court, billiards, pickleball, bocce and fitness center. Located close to shopping and restaurants, including the Smith Haven Mall.

201 Bentley Court E, Saint James

203 Cabot Court S, Saint James
$475,000
1 Beds ⋅ 1 Baths ⋅ 955663 MLS
Enjoy the condo lifestyle in this stunning, fully renovated, one-level condo in the Fairfield at St. James 55+ gated community featuring an open and beautifully updated kitchen with quartz countertops, oversized island, custom backsplash, abundant cabinetry, stainless steel appliances and a pantry closet, central air conditioning, hardwood floors, crown molding, recessed lighting, solar tubes, new luxury bathroom, new doors, fresh paint, two walk in closets, young washer and dryer, new extended paver patio with electric awning, taxes of only $2,198.10 after basic star and common charges of $302/month (including cable). Community amenities include clubhouse, an indoor pool, two outdoor pools, fitness center, library, billiards, tennis, bocce, pickleball and a scenic walking trail all in an unbeatable location near the Smith Haven Mall, with easy access to restaurants, shopping, and virtually every retailer and convenience imaginable. With everything updated and low taxes, low utilities, and low maintenance—low bills—this is easy living at its best. Come see for yourself.

203 Cabot Court S, Saint James

101 Flair Court E, Saint James
$475,000
1 Beds ⋅ 2 Baths ⋅ 954627 MLS
Beautifully Updated 1 Bedroom, 1.5 Bath Ranch Located In The Highly Sought-After 55+ Active Community at Fairfield Saint James. This Move In Ready Home Features A New White Kitchen W/Quartz Countertops, New Appliances, Full Size Washer Dryer, Modern Baths, Central Air Conditioning And New Vinyl Flooring Throughout. Additional Features Include Oversized Closets, Recessed Lighting, Generous Sized Rooms, Formal Dining Area & Den With Glass Sliders To Private Patio. Fairfield Saint James Is A Gated Community Offering A Vibrant Lifestyle With Numerous Activities: Clubhouse, Pool(s), Tennis/Pickleball, Gym, Sauna & Walking Trails Throughout. Conveniently Located Close To Restaurants, Parks & Shops. Offering A Shuttle Service To All. *Taxes $3,453

101 Flair Court E, Saint James

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.